


Lola

by JJ1564



Category: Supernatural
Genre: Blow Jobs, Drunk Sam, First Time, M/M, Stanford Era, Top Sam, Transvestite
Language: English
Status: Completed
Published: 2014-04-13
Updated: 2014-04-13
Packaged: 2018-01-19 06:19:33
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,679
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1459102
Author URL: https://archiveofourown.org/users/JJ1564/pseuds/JJ1564
Summary: <blockquote class="userstuff">
              <p>At Stanford, shy Sam wants to celebrate his 21st birthday in style and his friend Brady finds the perfect woman for him.</p>
            </blockquote>





	Lola

Sam’s stomach was so full of butterflies he was sure they would burst it open and fill the smoky air with color. He giggled at the image of butterflies swirling and fluttering around the crowded noisy bar.

‘You okay, kiddo?’ His friend Brady asked.

‘Yep. Butterflies. Nervous.’ Sam admitted, sitting heavily on the chair that Brady guided him to.

‘Fuck, you’re a real light-weight, ain’t you?’ Brady chuckled. ‘A few beers and you’re floating.’

‘Floating like a butterfly.’ Sam said, smiling dopily at his friend.

‘Well at least you’re a happy drunk.’ Brady glanced over at Jessica, who was looking around the bar with disdain. ‘Keep an eye on him, darlin'. I’m gonna get us some drinks.’

Jessica sat down next to Sam. ‘This place is a dive,’ she announced, ‘and Sam should be going home.  You know he’s not used to drinking.’

‘Aw, lighten up!’ Brady ruffled Sam’s thick hair and Sam grinned at him. ‘Tell Jessica you're alright, Sam.’

‘I’m fan-fucking-tastic, Jess-hic-Jessica," Sam slurred, ‘More beer!’

Brady headed off to the bar, chuckling to himself. Jessica pulled out her phone and checked her messages. She hated talking to drunk boys.

‘Brady’s gonna get me laid.’ Sam did a loud stage whisper and Jessica cringed as several pairs of eyes looked over at them. ‘I’ve never gone past first base, y’know.’

Jessica couldn’t help but laugh. Sam was a sweet boy and she was being a bitch to him. ‘I’m surprised, Sammy. You’re a good-looking boy.’

‘Thank you, ma’am!’ Sam saluted her.

‘So how on earth are you still a virgin?’ She leaned forward, stroking his knee.

‘I dunno. I’ve made out with girls, kissed ‘em and touched their…’ Sam giggled. ‘Touched their boobies, but I never….it’s never felt right. Going down there.’ He raised his eyebrows and gave a little shudder. Jessica’s mouth opened in surprise. She was sure from his reaction that he was probably gay, yet he didn’t seem to realize.

‘Perhaps you just haven’t met the right person.’ She said, letting her hand move up his leg to his groin and thrusting her ‘boobies’ towards him. Any red-blooded male would have reacted to her, but Sam just gave her a grin and slumped back in his chair.

‘You’re Brady’s girl.’ He said, pushing her hand away from his upper thigh.

‘And you’re a true gentleman.’ Jessica smiled at him. Brady returned with a tray of drinks and a very tall blonde woman, wearing a short black tight-fitting dress. Scratch that, it was a very pretty man wearing a short black tight-fitting dress, fish net stockings, high heels and a blonde wig. He had huge green eyes and his lashes would have been incredibly long even without mascara. His lips were full and pouty, with a light pink lipstick that made them look soft and inviting. Jessica had never seen a more beautiful man, or woman in fact.

‘This is…sorry what’s your name, sweetheart?’ Brady asked.

‘Lola.’ The man said, slipping into the chair next to Sam, who was looking at him with wide eyes and an open mouth.

‘You’ll catch flies, kiddo!’ Brady chuckled, nudging Sam’s shoulder.

‘Lola.’ Sam repeated, like someone in a daze.

‘What’s your name, honey?’ Lola asked, his voice soft and deep.

‘S-Sammy, Sam. Um, Sam.’ Sam said, never taking his eyes off of Lola.

‘Pleased to meet you, Sammy- Sam.’ Lola smiled and Sam carried on staring stupidly back.

‘Well, I think he likes you.’ Brady said, handing out the drinks.

‘Brady!’ Jessica hissed. ‘What the hell?’

‘She’s….so pretty….she’s perfect.’ Sam murmured, then blushed. ‘Sorry, I’m a little drunk.’

‘Don’t worry, Sammy-Sam.’ Lola purred and ran his manicured fingernails along Sam’s thigh, just as Jessica had done minutes before, but this time Sam’s eyes widened and his body stiffened.

‘Fuck….don’t….’ He groaned, ‘not….not here.’

Lola laughed and threw back his shot of whisky in one gulp. ‘Eager, much?’

‘Brady….’ Jessica glared at her boyfriend, ‘this isn’t right.’

‘Hey, sugar, I’ll be gentle with him.’ Lola winked at her.

Sam felt like his head was spinning and not just from the alcohol. ‘Oh shit,’ he moaned; he was hard, just from Lola’s fingers on his leg and he needed more. ‘I-I gotta get some air.’

‘I’ll come with you, Sammy-Sam.’ Lola stood up and helped Sam to his feet.

‘You’re real pretty, an’ you’re real tall for a girl.’ Sam slurred.

‘Brady, he doesn’t even realize….’ Jessica whispered and Brady shushed her.

‘Trust me, sweetheart. This is what he needs.’ Brady threw Sam’s apartment keys to Lola who caught them effortlessly.

Sam was aware of leaving the bar, of getting in a cab and arriving home, but he was unable to speak or think and was having trouble just breathing, This woman was so beautiful, so hot, just looking at her was doing things to his body he had never experienced before.

‘You okay, Sammy-Sam?’ Lola asked when they got through the front door.

‘Fuck…yeah.’ Sam lurched forward, trapping her against the wall, kissing her sloppily, vaguely surprised that in her heels she was the same height as him. This was a new experience, usually he had to bend down so low to kiss a girl it cricked his neck.

Lola brought her hands up to gently tug his hair and pull his face away. ‘Easy, Sammy-Sam. There’s no rush. We have all night.’

‘Fuck.’ Sam said again. ‘You…you mean?’

‘You have me all night. What do you want to do to me?’ Lola winked at him and licked her bottom lip slowly. Sam loved her deep, husky voice and her ridiculously full lips. But it was her eyes, so bright, so green and so sparkling...

‘Wanna….want everything.’ Sam kissed her again, more controlled this time. She opened her lips and let him slip his tongue inside her mouth, sucking on it and making his already hard cock even harder.

Sam ground his hips against hers and moved his hands round to caress her bottom. She held onto his hair and they kissed for a while until Sam had to part to take a deep breath and just look at her again.

‘You're so fucking beautiful.’ Sam moaned as he lifted her up. She grasped his shoulders and wrapped her legs around him. He carried her through to his bedroom and deposited her on the bed. Sam hesitated, unsure what to do now.

‘Let me help you relax, Sammy-Sam.’ Lola sat forward and undid the button on his jeans. Sam let out a noise that was almost a whimper. Lola grinned and unzipped him, pushing his jeans and boxers down and running her hand over his cock.

‘Oh, fuck,' Sam did whimper this time. ‘Please….please.’ He held onto Lola’s shoulders and watched in amazement as she started to lick the tip of his cock, still holding it in her large but gentle hand. Her other hand was holding his hip and when she moved it around to squeeze his ass, he gave a little yelp. ‘Lola...oh God,’ She licked the length of his cock and his hips started to move almost of their own accord. ‘Lola….please…’

She grinned up at him and kissed his cock-head, then licked it, opening her pretty pink lips wider as she started to take him inside her mouth. Sam had only ever got off on his own, under the covers of his bed or in the shower and having Lola’s hands and mouth on his cock was wonderful.

‘Fuck, yeah, oh God.’ He gasped as she took him deeper inside. She gagged and pulled off when his cock hit the back of her throat. ‘Shit, you okay?’

‘Don’t worry, Sammy-Sam.’ she gasped, ‘you’re a big boy. Girl’s gotta breath, y’know.’

Sam blushed. Surreptitious glances at other boys in changing rooms and men at urinals had led him to believe he was a little bigger than average. But then again he was 6’4” so most of him was bigger than average. Hearing Lola tell him he was big was a kinda nice surprise, though.  ‘Sorry.’

‘Never apologize for having a huge cock, Sammy-Sam. It’s a gift from God.’ Lola grinned and resumed sucking him. He came very quickly after that, as she fondled his balls and his ass. She pulled off just as he was about to come and guided his cock so that he spurted all over her face. She kept her eyes closed and her lashes were dripping with come.

Sam groaned and sank down onto his knees, unable to stand any longer. Lola blinked at him, smiling, her face wet and glowing. ‘That…you…amazing…’ Sam muttered, reaching out to stroke her face.

‘Come here,’ she opened her arms and Sam found himself wrapped in a tight hug. She released him too soon, pushing him away from her, then scrambling further up onto the bed. ‘I need a drink now.’ She said, pulling a tissue from inside her dress and wiping her face with it.

Sam stood up and watched her, trails of mascara now ran down from her eyes.  Her blonde hair was messed up and looked kinda wonky. Somehow, now she was dirty and disheveled, she looked even hotter.

‘Um, beer? Or water?’ Sam asked, heading for the door.

‘Both would be great.’ She smiled and laid back on the bed. ‘I think we’re going to work up quite a thirst, Sammy-Sam.’

Sam’s legs were shaking as he walked through to the kitchen, grabbing two bottles of beer and two of water. He carried them back and almost dropped them when he saw Lola lying back on the bed, her legs spread wide, rubbing her left hand over her black lace panties and running the fingers of her right hand over her bottom lip.

‘Fuck!’ Sam gasped, managing to hold onto the bottles and depositing them on the bedside cabinet. He needed to be inside this beautiful creature again, right now. 

‘You ready for me Sammy-Sam?’ Lola whispered. ‘Or do you need a little recharge time?’ She moved her right hand to cup his already half-hard cock.

‘Now…now…’ Sam groaned and sank onto his knees beside her. He reached out a trembling hand to move her hand away and stroke her pussy….’What the hell!’ He sat back, staring in amazement at the very large, very hard and very manly cock bulging inside the black lace.

‘Don’t you like me, Sammy-Sam?’ Lola pouted, taking Sam's hand and moving it over her – his – erection.

‘Fuck, shit.’ Sam groaned as he felt the hard, hot dick swelling beneath the scratchy lace.

‘Let’s move this along, shall we? Sammy-Sam. So, have you ever?’ Lola raised a perfect eyebrow; Sam shook his head, blushing a little in embarrassment. ‘Don’t worry, Sammy boy, I’m gonna make you a man.’

Sam’s head swam as Lola shimmied out of the panties, his cock fully erect now and straining up out of the confines of the lace. Sam was torn between gazing at his pretty pink cock and his pretty pink lips.

‘Take my dress off, Sammy; you can touch my nipples.’ Lola instructed. Sam pulled the tight dress over his head, revealing a tight black corset that finished just below his nipples.

‘Oh my God.’ Sam groaned. He reached out both hands, running them over Lola’s chest and stroking his nipples, loving the little gasps of pleasure from the man. ‘Wow.’ He ran his large hands down the corset and then over Lola’s thighs. Lola moaned and opened his legs wider.

‘Okay, Sammy-Sam. I’m ready.’ Lola said with a smile, as he stroked Sam’s cock. ‘You are too.’

Sam moved between Lola’s spread legs and ran his fingers over that pretty pink dick and then down, down to the hole that looked so small he couldn’t imagine his cock fitting inside.

Lola sensed his hesitation and pulled his legs up, opening his hole slightly. ‘Use your fingers, one at a time, to stretch me. Use the lube. Use your tongue too, if you like.’ Sam was sure he was going to pass out, his heart was beating so fast - he wanted to taste Lola, stretch him open and make him gasp again. He slipped his index finger inside the tight hole, glancing up at Lola to make sure he was okay.

‘S’alright, Sammy,’ Lola gave him an encouraging smile, ‘this ain’t my first rodeo. You won’t hurt me.’

‘Fuck.’ Sam groaned, unable to form any other words or string together a sentence. Lola chuckled then gasped as he added a second finger.

‘That’s it, yeah, move ‘em,’ Lola panted as Sam flexed his fingers, ‘yeah, that’s it. More.’

Sam added a third finger and twisted them; he had never felt anything so soft or silky or warm around his fingers and it was intoxicating. If his cock hadn’t been so fucking hard, he would have kept his fingers inside for longer, exploring, making Lola pant and squirm. And he wanted to taste too, to run his tongue around and inside, but his cock was winning the battle.

‘Fuck, gotta, gotta fuck you.’ Sam groaned as he pulled his hand free and lined up his cock at the now-slightly gaping hole. He picked up the lube and filled his palm, then ran his hand over his heavy cock. Lola groaned as he watched him and hitched his legs wider.

‘You’re fucking huge, Sammy-Sam.’ He bit his bottom lip and Sam saw a flicker of anxiety there. He looked so beautiful, his green eyes huge in his pale face, the corset resting just above his hips, making him look so feminine. His long legs were still covered in the fish-net stockings, and his large hands were wrapped around his knees. His hardening cock had a dribble of pre-come collecting at the tip.

‘We don’t have to…I mean…’ Sam held his own cock in his hand, knowing if Lola said no he would be coming soon anyway, just at the sight of her...him!

‘No, it’s okay Sammy-Sam. Fuck me, baby, fuck me now.’ Lola said. ‘Want you.’

Sam groaned and slid his cock through the tight ring. Lola gasped again and Sam knew he would sell his soul for the chance to make Lola gasp like this every day, every night, forever more. Sam wanted to go slow, wanted this to last. The feeling of Lola around him, moving in time with him, taking him deeper inside, was so incredible. But he was as hard as nails, and as soon as he was fully inside he knew he couldn’t hold out much longer.

‘Wait,’ Lola gasped; Sam thought he must be fucking joking, but he stilled to look in those expressive green eyes. ‘Make…make me come…it will feel good….for you.’

Sam chuckled and took Lola’s leaking cock in his fist, pumping it a few times. Lola groaned and arched his back; as promised it felt fucking amazing inside as his muscles clenched around Sam’s cock. Lola came with a guttural cry, spurting all over the corset covering his stomach and chest. Sam followed moments later, gripping Lola’s hips tightly as he emptied himself inside him.

Sam pulled out and flopped onto the bed next to Lola. He was running his hands through the come splayed over his corset, then held one up to Sam's lips. ‘Taste me.’ He whispered and Sam licked at his fingers, loving the salty bitter taste.

Sam sighed happily and moved up the bed, pulling Lola into his arms. His wig was half off and Sam removed it, running his fingers through the short, sweaty hair.

‘So, did you like your birthday present, Sammy-Sam?’

Lola asked.

‘Fuck, yeah. Best birthday ever. You are the best big brother in the world.’ Sam grinned as he kissed the top of Dean’s head.

Dean laughed, looking up at Sam. ‘I’m glad you heard that old song, Sammy. ‘Cause when you first said you wanted role-playing for your birthday, I expected geeky.’

‘But I wanted sexy.’ Sam chuckled. ‘And, Lola, you sure delivered.’

 

 

 

 

 

**Author's Note:**

> In this fic, I paired Brady with Jessica and set it before Dean had visited Sam there, so they don't know who he is. I didn't put Dean/Sam, roleplay or wincest in the tags as I hoped the identity of Lola wouldn't be obvious.


End file.
